Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides

ABSTRACT

The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.

The invention relates to novel pyrazolyl benzyl ethers, to a pluralityof processes for their preparation and to their use for controllingharmful organisms.

Certain compounds having a similar substitution pattern, and theirfungicidal action, are already known (WO 98/55461, WO 97/07103, WO96/10556, WO 96/06072, WO 99/33812, DE-A 4424788). However, the activityof these prior-art compounds is, in particular at low application ratesand concentrations, not entirely satisfactory in all areas of use.

This invention now provides the novel pyrazolyl benzyl ethers of thegeneral formula (I)

in which

A represents oxygen or —NH—,

R represents in each case optionally substituted alkyl, cycloalkyl oraryl,

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, in each caseoptionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinylor alkylsulphonyl.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkanediyl, alkenyl or alkinyl, are in each casestraight-chain or branched, including in combination with heteroatoms,such as, for example, in alkoxy, alkylthio or alkylamino.

Unless indicated otherwise, preference is given to hydrocarbon chainshaving 1 to 6 carbon atoms.

Aryl represents aromatic mono- or polycyclic hydrocarbon rings, such as,for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenylor naphthyl, in particular phenyl.

Heterocyclyl represents saturated or unsaturated and also aromaticcyclic compounds in which at least one ring member is a heteroatom, i.e.an atom different from carbon. If the ring contains a plurality ofheteroatoms, these can be identical or different. If the ring contains aplurality of oxygen atoms, these are not adjacent. Preferred heteroatomsare oxygen, nitrogen and sulphur. If appropriate, the cyclic compoundsform, together with further carbocyclic or heterocyclic fused-on orbridged rings, a polycyclic ring system. Preference is given to mono- orbicyclic ring systems, in particular to mono- or bicyclic aromatic ringsystems. A polycyclic ring system can be attached via the heterocyclicring or via a fused-on carbocyclic ring.

Cycloalkyl represents saturated carbocyclic compounds which, ifappropriate, form a polycyclic ring system together with furthercarbocyclic fused-on or bridged rings.

Furthermore, it has been found that the novel pyrazolyl benzyl ethers ofthe general formula (I) are obtained when

a) benzyl halides of the formula (II)

 in which

A, L¹, L², L³ and L⁴ are as defined above and

X represents halogen,

are reacted with a substituted pyrazolone of the general formula (III),

 in which

R is as defined above, if appropriate in the presence of a diluent andif appropriate in the presence of an acid acceptor, or when

b) pyrazolyl benzyl ethers of the formula (I) where A is oxygen arereacted with methylamine, if appropriate in the presence of a diluent.

Finally, it has been found that the novel pyrazolyl benzyl ethers of thegeneral formula (I) are highly active against harmful organisms andexhibit in particular very strong fungicidal and insecticidal action.

The active-compounds according to the invention may also, at certainconcentrations and application rates, exhibit activity against plantpests.

If appropriate, the compounds according to the invention can be presentas mixtures of different possible isomeric forms, in particular ofstereoisomers, such as, for example, E and Z. What is claimed are boththe E and the Z isomers, and any mixtures of these isomers.

The invention preferably provides compounds of the formula (I) in which

A represents oxygen or —NH—,

R represents alkyl having 1 to 8 carbon atoms,

represents cycloalkyl having 3 to 7 carbon atoms which is optionallymono- or disubstituted by halogen, alkyl or hydroxyl;

or represents phenyl or naphthyl, each of which is optionally mono- totetrasubstitued by identical of different substituents, where thepossible substituents are preferably selected from the list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl,alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbonatoms;

in each case straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

in each case straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

in each case straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy,alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in therespective hydrocarbon chains;

cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;

in each case doubly attached alkylene having 3 or 4 carbon atoms,oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2carbon atoms, each of which radicals is optionally mono- totetrasubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, oxo, methyl, trifluoromethyl andethyl;

or a group

 in which

A¹ represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms orcycloalkyl having 3 to 6 carbon atoms and

A² represents hydroxyl, amino, methylamino, phenyl, benzyl or representsin each case optionally cyano-, hydroxyl-, alkoxy-, alkylthio-,alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having ineach case 2 to 4 carbon atoms,

and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl,heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio, orheterocyclylalkyl having in each case 1 to 3 carbon atoms in therespective alkyl moities, each of which radicals is optionally mono- totrisubstituted in the ring moiety by halogen and/or straight-chain orbranched alkyl or alkoxy having 1 to 4 carbon atoms,

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, or representsalkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case 1 to 6 carbon atoms, each of which radicals is optionallysubstituted by 1 to 5 halogen atoms.

The invention relates in particular to compounds of the formula (I) inwhich

A represents oxygen or —NH—,

R represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,pentyl or hexyl, or represents cyclopentyl or cyclohexyl, each of whichis optionally mono- or disubstituted by fluorine, chlorine, methyl,ethyl or hydroxyl;

or represents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where thepossible substituents are preferably selected from the list below:

fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl,formyl, carboxyl, carbamoyl, thiocarbamoyl,

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-,neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-,4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-,3-, 4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl,hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,

methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, methylthiomethyl,ethylthiomethyl,

vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy,allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;

trifluoromethyl, trifluoroethyl,

difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, trifluoromethylthio,difluorochloromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl,

methylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino,

acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl,ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl,acryloyl, propioloyl,

cyclopentyl, cyclohexyl,

in each case doubly attached propanediyl, ethyleneoxy, methylenedioxy,ethylenedioxy, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting offluorine, chlorine, oxo, methyl and trifluoromethyl,

or a grouping

 where

A¹ represents hydrogen, methyl or hydroxyl and

A² represents hydroxyl, methoxy, ethoxy, amino, methylamino, phenyl,benzyl or hydroxyethyl, and

phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl,phenylethyl, phenylpropyl, benzyloxy, benzylthio,5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl,benzoxazol-2-yl-methyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl,oxadiazolyl, each of which is optionally mono- to trisubstituted in thering moiety by halogen and/or straight-chain or branched alkyl or alkoxyhaving 1 to 4 carbon atoms, and

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, fluorine, chlorine, bromine, cyano,nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl.

The invention relates in particular to compounds of the formula (I) inwhich

A represents oxygen or —NH—, or

R represents phenyl which is optionally mono- to tetrasubstituted byidentical or different substituents, where the possible substituents arepreferably selected from the list below:

cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, trifluoromethyl,

L¹ and L³ represent hydrogen and

L² and L⁴ independently of one another represent hydrogen or methyl.

In a further very particularly preferred group of compounds

L¹ and L³ represent hydrogen and

L² and L⁴ independently of one another represent hydrogen or methyl.

The general or preferred radical definitions given above apply both tothe end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

The radical definitions given in the respective combinations orpreferred combinations of radicals for these individual radicals are,independently of the combination of radicals given in each case, alsoreplaced by any radical definitions of other preferred ranges.

The formula (II) provides a general definition of the benzyl halidesrequired as starting materials for carrying out the process a) accordingto the invention. In this formula (II), A, L¹, L², L³ and L⁴ preferablyor in particular have those meanings which have already been mentionedin connection with the description of the compounds of the formula (I)according to the invention as being preferred or as being particularlypreferred for A, L¹, L², L³ and L⁴. X represents halogen, preferablychlorine or bromine.

The starting materials of the formula (II) are known and can be preparedby known processes (compare, for example, WO 97/07103, WO 96/10556, WO96/06072).

The formula (III) provides a general definition of the pyrazolonesfurthermore required as starting materials for carrying out the processa) according to the invention. In this formula (III), R preferably or inparticular has that meaning which has already been given in connectionwith the description of the compounds of the formula (I) according tothe invention as being preferred or as being particularly preferred forR.

The starting materials of the formula (III) are known and/or can beprepared by known methods (compare, for example, Chem. Pharm. Bull. 19,1389 (1971)).

The pyrazolyl benzyl ethers of the formula (I) where A is oxygenrequired as starting materials for carrying out the process b) accordingto the invention are compounds according to the invention and can beobtained according to process a).

The methylamine furthermore required as starting material for carryingout the process b) according to the invention is a generally customarychemical for synthesis.

Suitable diluents for carrying out processes a) and b) according to theinvention are all inert organic solvents. These preferably includealiphatic, alicyclic or aromatic hydrocarbons, such as, for examplepetroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decaline; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, dichloromethane,chloroform, carbon tetrachloride, dichloroethane or trichloroethane;ethers, such as, for example, diethyl ether, diisopropyl ether, methylt-butyl ether, methyl-t-amyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, 1,2-diethoxyethane or anisol; ketones, such as, forexample, acetone, butanone, methyl isobutyl ketone or cyclohexanone;nitriles, such as, for example, acetonitrile, propionitrile, n- ori-butyronitrile or benzonitrile; amides, such as, for example,N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphorictriamide; esters, such as,for example, methyl acetate, or ethyl acetate; sulphoxides, such as, forexample, dimethyl sulphoxide; sulphones, such as, for example,sulpholane, alcohols, such as, for example, methanol, ethanol, n- ori-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol,ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether,diethylene glycol monoethyl ether, mixtures thereof with water or purewater.

The process a) according to the invention is, if appropriate, carriedout in the presence of a suitable acid acceptor. Suitable acid acceptorsare all customary inorganic or organic bases. These preferably includealkaline earth metal or alkali metal hydrides, hydroxides or amides,alkoxides, acetates, carbonates or bicarbonates, such as, for example,sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammoniumhydroxide, sodium acetate, potassium acetate, calcium acetate, ammoniumacetate, sodium carbonate, potassium carbonate, potassium bicarbonate,sodium bicarbonate or ammonium carbonate, and also tertiary amines, suchas, for example, trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethyl-benzylamine, pyridine,N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloandecene (DBU).

When carrying out the process a) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures of from −20° C. to100° C., preferably at temperatures of from −10° C. to 80° C.

When carrying out the process b) according to the invention, thetemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures of from −20° C. to 100° C.,preferably temperatures of from −10 C. to 50° C.

For carrying out the process a) according to the invention for preparingcompounds of the formula (I), in general from 0.5 to 15 mol, preferablyfrom 0.8 to 8 mol, of substituted pyrazolone of the formula (III) areemployed per mole of the benzyl halide of the formula (II).

For carrying out the process b) according to the invention for preparingcompounds of the formula (I), in general from 1 to 50 mol, preferablyfrom 1 to 10 mol, of methylamine are employed per mole of the pyrazolylbenzyl ether of the formula (I) where A is oxygen.

The processes a) and b) according to the invention are generally carriedout under atmospheric pressure. However, it is also possible to operateunder elevated or reduced pressure—in general between 0.1 bar and 10bar.

The practice of the reaction and the work-up and isolation of thereaction products are carried out according to generally customarymethods (compare also the Preparation Examples).

The substances according to the invention have potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; andPseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention can be employedparticularly successfully for controlling cereal diseases, such as, forexample, against Erysiphe, Leptosphaeria or Puccinia species, diseasesin fruit and vegetable growing and viticulture, such as, for example,against Alternaria, Venturia Sphaerotheca and Plasmopara species, orrice diseases, such as, for example, against Pyricularia.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

If appropriate, the active compounds according to the invention can, atcertain concentrations and application rates, also be employed asherbicides, for regulating plant growth and for controlling animalpests. If appropriate, they can also be used as intermediates orprecursors in the synthesis of other active compounds.

The active compounds, being tolerated well by plants and havingfavourable homeotherm toxicity, are suitable for controlling animalpests, in particular insects, arachnids and nematodes, encountered inagriculture, in forests, in the protection of stored products andmaterials and in the hygiene sector. They can preferably be employed ascrop protection agents. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae and Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella occidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera devastatrix, Pemphigusspp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphumpadi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps,Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvatalugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. andPsylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp. and Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon soistitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp. and Brevipulpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp. and Bursaphelenchusspp.

They can be employed particularly successfully for controllingplant-damaging insects, such as, for example, against the larvae of themustard beetle (Phaedon cochleaviae), the green peach aphid (Myzuspersicae) and also plant-damaging nematodes, such as, for exampleMeloidogyne incognita.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be tackifiers, sizes, paper and board, textiles,leather, wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably tackifiers, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can as such or in theirformulations also be used in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of mixing components are the following:

Fungicides

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyidithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole, uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanoneO-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulphate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-hydrochloride,

ethyl[(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogen carbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alphacypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoat, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos, naled, nitenpyram, nithiazine, novaluron,

omethoat, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb,pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur, prothiofos,prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben,pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, suiprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyiidazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi, for example against Candida speciessuch as Candida albicans, Candida glabrata, Epidermophyton species, suchas Epidermophyton floccosum, Aspergillus species such as Aspergillusniger and Aspergillus fumigatus, Trichophyton species such asTrichophyton mentagrophytes, Microsporon species such as Microsporoncanis and audouinii. The list of these fungi does by no means limit themycotic spectrum which can be covered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

When used as insecticides, the active compounds according to theinvention can furthermore be present, in their commercial formulationsand in the use forms prepared from these formulations, as a mixture withsynergists. Synergists are compounds which enhance the activity of theactive compounds, without it being necessary for the added synergist tobe active itself.

The content of active compound in the use forms prepared from thecommercial formulations can vary within wide ranges. The concentrationof active compound of the use forms can be from 0.0000001 to 95% byweight of active compound and is preferably between 0.0001 and 1% byweight.

Application is carried out in a manner appropriate for the use forms.

When used against hygiene pests and pests of stored products, the activecompound has excellent residual activity on wood and clay and goodalkali stability on limed substrates.

PREPARATION EXAMPLES Example 1

5.3 g (0.0275 mol) of 1-(4-chlorophenyl)-1,2-dihydro-3H-pyrazol-3-one,10 g (0.0275 mol) of methyl2-[2-(bromomethyl)phenyl]-2-[(fluoromethoxy)imino]acetate (84% pure) and1.1 g (0.0275 mol) of sodium hydride (60%) in 40 ml of dry dimethylformamide are stirred at room temperature for 18 hours. The solvent isthen distilled off under reduced pressure. The residue is taken up in 50ml of ethyl acetate and washed repeatedly with water. The organic phaseis dried over sodium sulphate and concentrated under reduced pressure.The residue is chromatographed on silica gel using hexane/acetone (8:2).This gives 5 g (43.5% of theory) of methyl2-[2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]-2-[(fluoromethoxy)imino]acetate.

HPLC: logP=3.86

Example 2

4 g (0.007 mol) of methyl2-[2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)-phenyl]-2-[(fluoromethoxy)imino]acetateare dissolved in 30 ml of methanol, and about 0.7 g (0.02 mol) ofmethylamine is then introduced, whereupon the temperature of thesolution increases to about 30° C. This mixture is stirred at roomtemperature for 18 hours, and the solvent is then distilled off underreduced pressure. The residue is taken up in 50 ml of ethyl acetate andwashed repeatedly with water. The organic phase is dried over sodiumsulphate and again concentrated under reduced pressure. The residue ischromatographed on silica gel using hexane/acetone (8:2). This gives 1.8g (60.5% of theory) of2-[2-({[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]-2-[(fluoromethoxy)imino]-N-methylacetamide.

HPLC: logP=3.30

The compounds of the formula (I-a) listed in Table 1 below are obtainedanalogously to Examples 1 and 2 and in accordance with the details givenin the general process descriptions.

TABLE 1 Example R A logP  2 4-chlorophenyl NH 3.30  3 4-fluorophenyl NH2.91  4 4-(i-propyl)phenyl O 4.38  5 3-bromophenyl NH 3.39  64-bromophenyl NH 3.4  7 3,5-dichlorophenyl NH 3.93  8 2-chlorophenyl O3.53  9 4-cyanophenyl O 3.18 10 4-tolyl O 3.74 11 2,4-dichlorophenyl O4.09 12 2-bromophenyl O 3.54 13 4-bromophenyl O 3.98 14 phenyl O 3.4 153,5-dichlorophenyl O 4.52 16 3-bromophenyl O 3.98 17 4-fluorophenyl O3.47 18 phenyl NH 2.83 19 2,4-dichlorophenyl NH 3.5 20 2,4-dichloro-4- O4.19 trifluoromethylphenyl 21 4-t-butylphenyl O 4.63 22 2-chlorophenylNH 2.96 23 4-t-butylphenyl NH 4.04 24 2,4-dichloro-4- NH 3.62trifluoromethylphenyl 25 2-fluorophenyl O 3.51 26 2,4-difluorophenyl O3.52 27 2,3-dichlorophenyl O 3.9 28 3,4-dimethylphenyl O 3.92 292,5-dichlorophenyl O 4.5 30 3-tolyl O 3.73 31 3-tolyl NH 3.15 322-fluorophenyl NH 2.93 33 2,4-difluorophenyl NH 3.02 342,3-dichlorophenyl NH 3.31 35 3,4-dimethylphenyl NH 362,5-dichlorophenyl NH 3.43 37 3-chlorophenyl O 3.88 384-(i-propyl)phenyl NH 3.83 39 4-methylphenyl O 3.74 40 4-cyanophenyl O3.18 41 4-methylphenyl NH 3.14 42 4-cyanophenyl NH 2.64 433-chlorophenyl NH 3.3

The logP values were determined in accordance with EEC Directive 79/831Annex V.A8 by HPLC (gradient method, acetonitrile/0.1% aqueousphosphoric acid).

USE EXAMPLES Example A

Erysiphe Test (barley)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substance according to the invention listed in Example(2) exhibits, at an application rate of 250 g/ha, an efficacy of 98% ormore.

Example B

Puccinia Test (wheat)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substance according to the invention listed in Example(1) exhibits, at an application rate of 250 g/ha, an efficacy of 98% ormore.

Example C

Puccinia Test (wheat)/curative

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours. Theplants are then sprayed with the preparation of active compound at thestated application rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substance according to the invention is given inExample (2) exhibits, at an application rate of 250 g/ha, an efficacy of98% or more.

Example D

Plasmopara Test (Grape vine)/protective

Solvent; 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, the young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabinet at about 20° C. and 100% relative atmospheric humidity for 1day. The plants are then placed in a greenhouse at about 21° C. andabout 90% relative atmospheric humidity for 5 days. The plants are thenmoistened and placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed in theExamples (1, 2, 3, 4, 5, 6, 7, 8, 11, 13, 14, 15, 16, 17, 18, 19, 26,27, 28 and 31) exhibit, at an application rate of 100 g/ha, an efficacyof 95% or more.

Example E

Sphaerotheca Test (cucumber)/protective

Solvent; 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedin a greenhouse at about 23° C. and a relative atmospheric humidity ofabout 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed in theExamples (1, 2, 3, 4, 5, 6, 7, 8, 11, 13, 14, 15, 16, 17, 18, 19, 26,27, 28 and 31) exhibit, at an application rate of 100 g/ha, an efficacyof 93% or more.

Example F

Venturia Test (apple)/protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and about 100%relative atmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and relativeatmospheric humidity of about 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed in theExamples (1, 2, 3, 4, 5, 6, 7, 8, 11, 13, 14, 15, 16, 17, 18, 19, 26,27, 28 and 31) exhibit, at an application rate of 10 g/ha, an efficacyof 98% or more.

Example G

Pyricularia Test (rice)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide

Emulsifier: 1.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Pyricularia oryzae and then remain at 100% rel.atmospheric humidity and 26° C. for 24 h. The plants are then placed ina greenhouse at 80% rel. atmospheric humidity and a temperature of 26°C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (1, 2) exhibit, at an application rate of 125 g/ha, an efficacyof 60% or more.

Example H

Alternaria Test (tomato)/protective

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young tomato plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Alternaria solani and then remain at 100% rel. atmospheric humidityand 26° C. for 24 h. The plants then remain at 96% rel. atmospherichumidity and a temperature of 20° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (1, 2) exhibit, at an application rate of 750 g/ha, an efficacyof 80% or more.

Example I

Leptosphaeria nodorum Test (wheat)/protective

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young wheat plants are sprayed with thepreparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with an aqueous sporesuspension of Leptosphaeria nodorum and then remain at 100% rel.atmospheric humidity and 20° C. for 48 h. The plants are then placed ina greenhouse at 80% rel. atmospheric humidity and a temperature of 22°C.

Evaluation is carried out 12-14 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention listed inExamples (1, 2) exhibit, at an application rate of 750 g/ha, an efficacyof 94% or more.

Example J

Phaedon Larvae Test

Solvent: 30 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, the substance according to the invention listed in Example(1) exhibits, at a concentration of active compound of 1000 ppm, a killrate of 100%.

Example K

Myzus Test

Solvent: 30 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the stated amount of emulsifier, and the concentrate isdiluted with emulsifier-containing water to the desired concentrations.

Broad bean seedlings (Vicia faba) infested by the green peach aphid(Myzus persicae) are dipped into a preparation of active compound of thedesired concentration and placed in a dish made of plastic.

After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

In this test, the substance according to the invention listed in Example(1) exhibits, at a concentration of active compound of 1000 ppm, a killrate of 95%.

What is claimed is:
 1. A compound of the Formula (I),

wherein A represents oxygen or —NH—, R represents in each caseoptionally substituted alkyl, cycloalkyl or aryl, L¹, L², L³ and L⁴ areidentical or different and independently of one another each representshydrogen, halogen, cyano, nitro, in each case optionallyhalogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl oralkylsulphonyl.
 2. The compound of the Formula (I) according to claim 1,wherein A represents oxygen or —NH—, or R represents alkyl having 1 to 8carbon atoms, represents cycloalkyl having 3 to 7 carbon atoms which isoptionally mono- or disubstituted by halogen, alkyl or hydroxyl; orrepresents phenyl or naphthyl, each of which is optionally mono- totetrasubstitued by identical or different substituents, where thesubstituents are optionally selected from the group consisting of:halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl; in each case straight-chain or branched alkyl,hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl,dialkoxyalkyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case 1 to 8 carbon atoms; in each case straight-chain or branchedalkenyl or alkenyloxy having in each case 2 to 6 carbon atoms; in eachcase straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms; in each case straight-chain or branchedhalogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbonatoms and 1 to 11 identical or different halogen atoms; in each casestraight-chain or branched alkylamino, dialkylamino, alkylcarbonyl,alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy,alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in therespective hydrocarbon chains; cycloalkyl or cycloalkyloxy having ineach case 3 to 6 carbon atoms; in each case doubly attached alkylenehaving 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms ordioxyalkylene having 1 or 2 carbon atoms, each of which radicals isoptionally mono- to tetrasubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,oxo, methyl, trifluoromethyl and ethyl; or a group

 wherein A¹ represents hydrogen, hydroxyl or alkyl having 1 to 4 carbonatoms or cycloalkyl having 3 to 6 carbon atoms and A² representshydroxyl, amino, methylamino, phenyl, benzyl or represents in each caseoptionally cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-,dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbonatoms, or represents alkenyloxy or alkinyloxy having in each case 2 to 4carbon atoms, and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio,or heterocyclylalkyl having in each case 1 to 3 carbon atoms in therespective alkyl moities, each of which radicals is optionally mono- totrisubstituted in the ring moiety by halogen and/or straight-chain orbranched alkyl or alkoxy having 1 to 4 carbon atoms, L¹, L², L³ and L⁴are identical or different and independently of one another eachrepresents hydrogen, halogen, cyano, nitro, or represents alkyl, alkoxy,alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6carbon atoms, each of which radicals is optionally substituted by 1 to 5halogen atoms.
 3. The compounds of the Formula (I) according to claim 1,wherein A represents oxygen or —NH—, R represents methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, pentyl or hexyl, or representscyclopentyl or cyclohexyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl; orrepresents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where thesubstituents are optionally selected from the group consisting of:fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl,formyl, carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-,4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4-, 5-(2-methyl-pentyl),1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4-(2,2-dimethylbutyl),1-, 2-(2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl,methoxymethyl, dimethoxymethyl, methoxy, ethoxy, n- or i-propoxy,methoxymethyl, ethoxymethyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,methylthiomethyl, ethylthiomethyl, vinyl, allyl, 2-methylallyl,propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy,propen-1-yloxy, crotonyloxy, propargyloxy; trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl,ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl,acryloyl, propioloyl, cyclopentyl, cyclohexyl, in each case doublyattached propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy, eachof which is optionally mono- to tetrasubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, oxo, methyl and trifluoromethyl, or a grouping

 wherein A¹ represents hydrogen, methyl or hydroxyl and A² representshydroxyl, methoxy, ethoxy, amino, methylamino, phenyl, benzyl orhydroxyethyl, and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio,5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl,benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl,oxadiazolyl, each of which is optionally mono- to trisubstituted in thering moiety by halogen and/or straight-chain or branched alkyl or alkoxyhaving 1 to 4 carbon atoms, and L¹, L², L³ and L⁴ are identical ordifferent and independently of one another each represents hydrogen,fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonylor ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl.
 4. The compoundsof the Formula (I) according to claim 1, wherein A represents oxygen or—NH—, or R represents phenyl which is optionally mono- or disubstitutedby identical or different substituents, where the substituents areoptionally selected from the: cyano, fluorine, chlorine, bromine,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,L¹ and L³ represent hydrogen and L² and L⁴ independently of one anotherrepresent hydrogen or methyl.
 5. A process for preparing the compound ofthe Formula (I) as defined in claim 1, comprising the step of: a)reacting a compound of the Formula (II)

 wherein A, L¹, L², L³ and L⁴ are as defined in claim 1 and X representshalogen, with a compound of the Formula (III),

 wherein R is as defined in claim 1, optionally in the presence of adiluent and optionally in the presence of an acid acceptor, or that b) acompound of the Formula (I) wherein A is oxygen, is reacted withmethylamine, optionally in the presence of a diluent.
 6. A compositionfor controlling harmful organisms, comprising one or more extendersand/or carriers and, optionally, surfactants, and at least one compoundas defined in claim
 1. 7. A method for controlling harmful organisms,comprising the step of allowing an effective amound of a compound asdefined in claim 1 to act on harmful organisms and/or their habitat. 8.A process for preparing a composition as defined in claim 6, comprisingthe step of mixing a compound as defined therein with one or moreextenders and/or carriers and/or surfactants.